Classifications

• • C—CHEMISTRY; METALLURGY
  • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
  • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
  • C11B9/00—Essential oils; Perfumes
  • C11B9/0007—Aliphatic compounds
  • C11B9/0011—Aliphatic compounds containing S
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/202—Aliphatic compounds
  • A23L27/2022—Aliphatic compounds containing sulfur
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/20—Synthetic spices, flavouring agents or condiments
  • A23L27/203—Alicyclic compounds
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides

Definitions

• ABSTRACT The preparation and use of the novel 3,7-dimethyl- 0cta-2,6-dienyl-rnercaptan as a new odorant and flavorant is disclosed.
• the invention relates to a new odorant and/or aroma substance, namely 3,7-dimethyl-octa-2,6- dienylmercaptan (thiogeraniol) having the formula
• the invention also relates to a process for the manufacture of the compound I, its use as an odorant or its use for aromatizing foodstuffs and/or delicacies and odorant compositions or foodstuffs, delicacies and/or aromatizing agents, characterized by a content of the compound I effective for olfactory and flavoring purposes.
• Formula I is intended to include both of the possible cis-trans isomers.
• the novel compound (I) in accordance with this invention can be obtained by treating a compound of the formula I S-R wherein R signifies a residue which can be cleaved off by hydrolysis. with a basev DESCRIPTION OF THE PREFERRED EMBODIMENTS
• starting materials I] in which the residue R is (preierred) Ila is used as the starting substance.
• the treatment with the base is expediently effected in aqueous medium.
• the reaction temperature can lie between about and 110C. A preferred temperature range is that from -30C.
• the compound of formula Ila can be obtained by bringing a geranylthiouronium halide NH Z , III
• Z signifies halogen, preferably geranylthiouronium bromide, to reaction with p-toluenesulphonic acid or a reactive derivative thereof in the usual and known manner.
• the compound of formula III can, in its turn, be obtained by reacting linalool or geraniol with hydrogen halide, preferably hydrogen bromide, in the presence of thiourea.
• hydrogen halide preferably hydrogen bromide
• reaction of linalool or geraniol with, for example, hydrogen bromide is expediently effected at to 100C, preferably at 10 to C.
• a halogen compound of formula III (preferably the bromide) can also serve as the starting material.
• a compound of formula III manufactured in situ can also be reacted under the influence of a base to give a compound I, for example by reacting a halide IV with thiourea in'a high-boiling solvent, for example triethyleneglycol.
• a high-boiling solvent for example triethyleneglycol.
• the reaction mixture containing the compound of formula III is treated with a high-boiling amine (e.g. triethylenepentamine), the thiouronium halide III being saponified to the compound I (cf Cossar et al., J. Org. Chem. 27, 93-95 (1962)).
• the compound of formula I (thiogeraniol) in accordance with this invention particularly possesses aroma and odorant properties, especially interesting berry notes as well as an interesting grape fruit note. It can accordingly be used for aromatizing foodstuffs and dc]- icacies as well as drinks or as an odorant for the manufacture of odorant compositions such as perfumes, or can find use for perfuming technical or cosmetic products of all kinds, for example solid and liquid detergents, synthetic washing agents, aerosols, soaps, creams, lotions.
• the novel compound I finds use in perfumery on the basis of its warm,..earthy,,spicy, green, slightly sulphurous note and its good-adhesivenes's. It is especially suitable in the manufacture of perfume bases with lavender-like notes.
• the fragrance characteristic of such bases is modified in an advantageous manner by the addition of the thiol in accordance with this invention.
• the content of the novel compound I in odorant compositions or in the perfumed products can vary within wide limits, for example between about 0.001 and about 5 wt. preferably between about 0.01 and about 1 wt.
• the flavor of the compound I can be designated as greenish. spicy and woody.
• the compound may be used in the manufacture of certain artificial fruit aromas, especially in the manufacture of cassis aroma (aroma of blackcurrants). Here it can especially find use as an aroma component in the manufacture of cheap synthetic buccu leaf oil.
• Natural buccu leaf oil which has hitherto found use as an aroma component for the production of cassis aroma is expensive and its price constantly climbs, as the demand exceeds the supply.
• readily accessible raspberry aromas of natural origin can also be changed into cassis aromas by addition of thiogeraniol. An addition of about 0.05-0.5%, preferably 0.2% of thiogeraniol is sufficient for this.
• the new compound of formula I can accordingly be used for producing cassis aromas in foodstuffs (e.g. milk drinks, yoghurt, etc.), in delicacies (e.g. confectionery products such as bon-bons, soft ice, etc.) and in drinks (e.g. mineral waters, syrups).
• foodstuffs e.g. milk drinks, yoghurt, etc.
• delicacies e.g. confectionery products such as bon-bons, soft ice, etc.
• drinks e.g. mineral waters, syrups.
• a suitable dosage includes, for example, the range of 10 ppb-lOO ppm,
• the compound I is of special flavorous interest, as
• EXAMPLE l 190 g. of geranylthiouronium tosylate are introduced into a solution of 60 g. of sodium hydroxide in 250 ml. of water and the mixture is stirred for two hours.
• the resulting thiogeraniol is removed from the alkaline emulsion by steam-distillation, taken up in 2 liters of ether, the ethereal solution is washed neutral three times with 200 ml. of saturated common salt solution each time, thereupon dried over anhydrous magnesium sulphate and the ether evaporated in vacuum.
• the resulting crude product displays the following composition:
• the geranylthiouronium tosylate used as the starting material can be obtained as follows:
• EXAMPLE 3 A natural raspberry aroma consisting of parts by weight of raspberry distillate, 400 parts by weight of raspberry juice concentrate and 100 parts by weight of sugar syrup is treated with 0.2 parts by weight of thiogeraniol. The original raspberry aroma thereby obtains the typical cassis note and can now find use as a cassis aroma.
• thiogeraniol 1% in phthalic
• thiogeraniol 1% in phthalic
• the addition of the thiogeraniol imparts to the lavender composition a greener and more herby fragrance.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Engineering & Computer Science (AREA)
• Life Sciences & Earth Sciences (AREA)
• Polymers & Plastics (AREA)
• Food Science & Technology (AREA)
• Health & Medical Sciences (AREA)
• Nutrition Science (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Oil, Petroleum & Natural Gas (AREA)
• Wood Science & Technology (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Fats And Perfumes (AREA)
• Seasonings (AREA)
• Cosmetics (AREA)

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Related Child Applications (1)

Publications (1)

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Cited By (3)

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Citations (2)

• 1971
  • 1971-05-27 CH CH777271A patent/CH550154A/xx not_active IP Right Cessation
• 1972
  • 1972-05-03 DE DE2221626A patent/DE2221626B2/de active Granted
  • 1972-05-04 IT IT197223908A patent/IT954977B/it active
  • 1972-05-08 US US251060A patent/US3896175A/en not_active Expired - Lifetime
  • 1972-05-24 BR BR3258/72A patent/BR7203258D0/pt unknown
  • 1972-05-25 NL NL727207058A patent/NL153523B/xx not_active IP Right Cessation
  • 1972-05-26 FR FR7218991A patent/FR2166849A5/fr not_active Expired
  • 1972-05-26 CA CA143,128A patent/CA983050A/en not_active Expired
  • 1972-05-26 JP JP7252401A patent/JPS5216090B1/ja active Pending
  • 1972-05-26 GB GB2498272A patent/GB1352968A/en not_active Expired
  • 1972-05-26 BE BE784016A patent/BE784016A/xx not_active IP Right Cessation
• 1976
  • 1976-12-14 JP JP15025376A patent/JPS5282734A/ja active Granted

Patent Citations (2)

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